This invention concerns a novel fragrance material, and perfumes and perfumed products comprising the novel material.
Cedar wood (heartwood of Eastern Red Cedar, i.e. Juniperus virginiana) has long been used as material for constructing or lining domestic storage spaces such as closets and chests. The wood is desirable for this purpose not only for its appearance but for its high content of an oil that consists primarily of a complex mixture of sesquiterpenoids. This oil gives cedar wood a characteristic and very pleasant fragrance, and it is also believed to act as a repellant to clothes moths. One problem with installed cedar wood is that its fragrance decreases markedly with time.
Cedarwood oil is produced commercially in large quantities by steam distillation of the heartwood of several members of the plant family Cupressaceae, particularly Juniperus virginiana and Juniperus ashei(in the U.S.A.), and of Cupressus funebris (in China). The oil is primarily used as a raw material in the fragrance industry, either in unmodified form or, more typically, after rectification and/or some chemical reaction to improve its fragrance characteristics. A solution of the oil, or modified forms thereof, is also marketed for temporarily restoring the fragrance of installed cedar wood.
The unmodified commercial oils, and rectified fractions thereof, have the disadvantage that they vary significantly in odor quality and character, depending on the source tree species and distillation and rectification methods used.
Another disadvantage of commercial cedarwood oils, and rectified fractions thereof, is that their odor impact is rather weak. This necessitates using fairly high percentages, typically around 10% or more, in perfume compositions to achieve a useful contribution to the fragrance. Furthermore, even at such concentrations, the cedar wood fragrance note is not very effectively imparted.
A further disadvantage of commercial cedarwood oils, and rectified fractions thereof, is that they may undergo undesirable chemical change during storage due to the action of light, moisture, and oxygen on carbon-carbon double bonds or susceptible functional groups of compounds in such oils or rectified fractions.
Previously-developed chemical treatments to enhance the fragrance utility of cedarwood oil, or rectified fractions thereof, include methylation, to produce mixtures rich in methyl cedryl ether (U.S. Pat. No. 3,373,208 to Blumenthal); acetylation, to produce mixtures rich in cedryl acetate or methyl cedryl ketone (U.S. Pat. No. 3,799,987 to Kitchens et al.); and oxidation, to produce mixtures rich in cedrene epoxide. These products, though useful fragrance materials, have odors that depart significantly from that of cedar wood. Thus the odor of methyl cedryl ether is characterized as “woody-amber”; that of methyl cedryl ketone as “musk-woody”; that of cedrene epoxide as “woody-amber-camphor”; that of cedryl acetate as “woody-vetiver”.
Other synthetic fragrance compounds have odors with a cedarwood note but that likewise depart significantly from the odor of cedar wood itself. For example: (S)-alpha-ionone (“cedarwood, raspberry”); 1-(4,8-cyclododecadienyl)-1-propanone (“cedarwood, amber, pepper”—U.S. Pat. No. 6,551,988 to Munro); (−)-(1′R,2S)-2-methyl-4-(2′,2′,3′-trimethyl-3′-cyclopenten-1′-yl)-4-penten-1-ol (“sandalwood; cedar”—U.S. Pat. No. 5,696,075 to Chapuis and Blanc).
In the fragrance industry there is ongoing need to develop new fragrance materials to give perfumers and other persons in the art the ability to create new perfumes, air fresheners, candles, colognes, personal care products, etc. The particular fragrance character of cedar wood is considered very desirable.
Thus, there is need for new fragrance materials that more closely resemble the odor of cedar wood, that effectively impart their odor to perfume compositions at lower concentrations, and that are more stable, compared with existing fragrance materials.